Discover Your Perfect Windsor Vacation Homes

Best Vacation Homes in Windsor

10.0 (11 Reviews)
Bed & Breakfast
Harbour House Inn B&B
  • Air Conditioner
  • Parking
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Windsor Luxury Rentals

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Windsor Pet Friendly Vacation Rentals

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Windsor Large Vacation Homes

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Why Choose Rent By Owner for your Windsor Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Windsor

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the region’s shoulder seasons when the area offers a quieter atmosphere and pleasant weather, perfect for exploring the local surroundings at your own pace.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences warm weather that makes it ideal for outdoor activities and exploring the scenic beauty of the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn attracts visitors seeking the vibrant fall foliage and mild weather, perfect for outdoor adventures and sightseeing in this region.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter months bring colder temperatures and quieter surroundings, making it a peaceful time to enjoy cozy accommodations in the area.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Early spring offers fewer visitors and cooler weather, providing a tranquil setting for exploring the natural beauty as everything begins to bloom again.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windsor

How to Book Your Windsor Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windsor

More Top-Rated Vacation Rentals in Windsor Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for relaxing meals amidst the region's scenic beauty.
  • Take advantage of spacious patios or decks to unwind while soaking up the fresh air.
  • Benefit from private gardens or landscaped yards that offer a peaceful outdoor retreat.
  • Make use of the outdoor fire pits for cozy evenings under the stars.
  • Utilize well-maintained grilling stations ideal for barbecues in this charming destination.
  • Explore nearby walking trails or lush green spaces connected to your rental property.
  • Relax by outdoor swimming pools available at select properties in this inviting area.

Top Attractions Around Windsor

What attractions are nearby?

In this destination, you'll find a variety of outdoor activities and cultural experiences nearby to enhance your stay in Windsor, Massachusetts, USA, making it an ideal choice for exploring the region’s natural beauty and local heritage.

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Family Activities

  • Windsor Historic Site Tour: Explore this area's rich history through engaging guided tours that bring its past to life for visitors of all ages.
  • Local Nature Trails and Parks: Discover scenic walking and biking paths in the region, perfect for family outings and outdoor adventures.
  • Family-Friendly Museums: Visit museums in the area featuring interactive exhibits and educational programs designed to captivate children and adults alike.
  • Seasonal Community Events: Experience local festivals and fairs held throughout the year that provide fun activities for the entire family in here.
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Adult Activities

  • Windsor Historic Site Tours: Dive into the area's rich history by exploring local sites that offer fascinating insights into its past.
  • Outdoor Activities at State Parks: Enjoy scenic hiking, picnicking, or birdwatching in nearby state parks that showcase the natural beauty of the region.
  • Wine and Brew Tasting Experiences: Indulge in tasting sessions at local wineries and breweries to appreciate the region's craft beverage scene.
  • Art Galleries and Cultural Events: Discover vibrant art galleries and participate in cultural events that highlight the area's creative spirit.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of nearby natural parks and cultural sites to fully immerse yourself in the regional charm during your stay.
  • Plan Ahead for Seasonal Events: Check the event calendar to experience seasonal festivals or outdoor activities that showcase the area’s unique community spirit.
  • Choose a Well-Located Accommodation: Select a vacation rental close to key points of interest to maximize your time exploring rather than commuting.
  • Enjoy Local Cuisine: Sample regional flavors at local eateries to enrich your experience and gain authentic insight into this destination’s culinary scene.

Transportation Options

  • Windsor Transit Service: This local transit option provides convenient transportation within the area, making it easy for you to explore nearby attractions from your vacation rental.
  • Regional Bus Lines: Connecting Windsor to surrounding regions, these bus services are a reliable choice for day trips and travel beyond the immediate destination.
  • Rental Car Services: With various rental agencies available locally, you can easily get around here at your own pace, ensuring seamless access to all that this destination offers.
  • Private Shuttle Services: For a comfortable and personalized travel experience, private shuttles operate regularly, providing direct routes to prominent locations in the region.

Local Customs Options

  • Welcoming Local Gatherings: Community events and gatherings are a cherished tradition here, offering you a chance to connect with locals and experience authentic regional hospitality.
  • Respect for Nature and Outdoors: The area values environmental preservation, so you'll find that outdoor activities often emphasize sustainability and respect for the natural landscape.
  • Historical Appreciation: Here, there's a deep reverence for history, reflected in local customs that honor the region’s heritage and historical sites.
  • Festive Seasonal Celebrations: Throughout the year, seasonal festivals and celebrations are common, providing an inviting atmosphere to enjoy regional culture and traditions.

Frequently Asked Questions About Windsor?

1. What are the top vacation rentals in Windsor?

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:

2. How many vacation rentals have private pools in Windsor?

There are 6 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windsor are best for families?

If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:

4. How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 228 in the Windsor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor. 

5. What is the cancellation policy for vacation rentals in Windsor, Massachusetts?

Cancellation policies vary depending on the property owner and listing. You should review the specific cancellation terms detailed on the property listing before booking or contact the host directly for clarification.

6. Are there any additional fees I should be aware of when booking a vacation rental in Windsor, Massachusetts?

Additional fees such as cleaning charges, service fees, or security deposits are typically outlined in the listing details. It’s advisable to read each listing carefully or reach out to the owner to understand all potential costs.

7. How do I find the best vacation rental options in Windsor, Massachusetts?

You can filter your search based on your preferences, including price range, amenities, and guest capacity. Reading reviews and checking the property descriptions will help you select the most suitable rental here.

8. What amenities are usually included in vacation rentals in this region?

Most rentals offer essential amenities like Wi-Fi, parking, and kitchen facilities. Specific offerings such as pools or outdoor spaces are listed on each property page, so review the details to ensure they meet your needs.

9. How do I contact the property owner if I have questions about my stay in Windsor, Massachusetts?

You can contact the owner directly through the messaging feature on the listing platform. This allows you to ask specific questions about the property, availability, or any special requirements you might have.